JP2022132332A - ヒドロシリル化-硬化性シリコーン組成物 - Google Patents
ヒドロシリル化-硬化性シリコーン組成物 Download PDFInfo
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- JP2022132332A JP2022132332A JP2022108399A JP2022108399A JP2022132332A JP 2022132332 A JP2022132332 A JP 2022132332A JP 2022108399 A JP2022108399 A JP 2022108399A JP 2022108399 A JP2022108399 A JP 2022108399A JP 2022132332 A JP2022132332 A JP 2022132332A
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- Prior art keywords
- hydrosilylation
- composition
- component
- groups
- curable silicone
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 63
- -1 maleate compound Chemical class 0.000 claims abstract description 60
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 19
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 11
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 11
- 229910052684 Cerium Inorganic materials 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical class C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 5
- 125000005372 silanol group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052693 Europium Inorganic materials 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910004283 SiO 4 Inorganic materials 0.000 description 3
- 229910004738 SiO1 Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910020485 SiO4/2 Inorganic materials 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical class C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 2
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000001010 compromised effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- GRGVQLWQXHFRHO-AATRIKPKSA-N (e)-3-methylpent-3-en-1-yne Chemical compound C\C=C(/C)C#C GRGVQLWQXHFRHO-AATRIKPKSA-N 0.000 description 1
- KNIBYEXSDVPWDA-ARJAWSKDSA-N (z)-4-(1-methoxypropan-2-yloxy)-4-oxobut-2-enoic acid Chemical compound COCC(C)OC(=O)\C=C/C(O)=O KNIBYEXSDVPWDA-ARJAWSKDSA-N 0.000 description 1
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 1
- FDNBQVCBHKEDOJ-FPLPWBNLSA-N (z)-4-(6-methylheptoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)CCCCCOC(=O)\C=C/C(O)=O FDNBQVCBHKEDOJ-FPLPWBNLSA-N 0.000 description 1
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical class C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- BJPGHILWNPIMKU-UHFFFAOYSA-N 2,4,6,8-tetrakis(hex-1-enyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CCCCC=C[Si]1(C)O[Si](C)(C=CCCCC)O[Si](C)(C=CCCCC)O[Si](C)(C=CCCCC)O1 BJPGHILWNPIMKU-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- HMVBQEAJQVQOTI-UHFFFAOYSA-N 3,5-dimethylhex-3-en-1-yne Chemical compound CC(C)C=C(C)C#C HMVBQEAJQVQOTI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- KYTGWYJWMAKBPN-UHFFFAOYSA-N [dimethyl(prop-2-enyl)silyl]oxy-dimethyl-prop-2-enylsilane Chemical compound C=CC[Si](C)(C)O[Si](C)(C)CC=C KYTGWYJWMAKBPN-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GVTGUOINIMHIRT-WAYWQWQTSA-N bis(1-methoxypropan-2-yl) (z)-but-2-enedioate Chemical compound COCC(C)OC(=O)\C=C/C(=O)OC(C)COC GVTGUOINIMHIRT-WAYWQWQTSA-N 0.000 description 1
- JSAYQGVHWNBMNG-UHFFFAOYSA-N bis(2-methylbut-3-yn-2-yloxy)-prop-1-enylsilane Chemical compound CC=C[SiH](OC(C#C)(C)C)OC(C#C)(C)C JSAYQGVHWNBMNG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- HZMBANJECWHRGE-GNOQXXQHSA-K cerium(3+);(z)-octadec-9-enoate Chemical compound [Ce+3].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O HZMBANJECWHRGE-GNOQXXQHSA-K 0.000 description 1
- GGVUYAXGAOIFIC-UHFFFAOYSA-K cerium(3+);2-ethylhexanoate Chemical compound [Ce+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O GGVUYAXGAOIFIC-UHFFFAOYSA-K 0.000 description 1
- WWLPQKCJNXAEFE-UHFFFAOYSA-K cerium(3+);dodecanoate Chemical compound [Ce+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O WWLPQKCJNXAEFE-UHFFFAOYSA-K 0.000 description 1
- BTVVNGIPFPKDHO-UHFFFAOYSA-K cerium(3+);octadecanoate Chemical compound [Ce+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O BTVVNGIPFPKDHO-UHFFFAOYSA-K 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- RQCQBDUYEHRNPP-UHFFFAOYSA-N dimethyl-bis(2-methylbut-3-yn-2-yloxy)silane Chemical compound C#CC(C)(C)O[Si](C)(C)OC(C)(C)C#C RQCQBDUYEHRNPP-UHFFFAOYSA-N 0.000 description 1
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 1
- MAHDKHLSBQARSK-NXVVXOECSA-N dioctan-3-yl (z)-but-2-enedioate Chemical compound CCCCCC(CC)OC(=O)\C=C/C(=O)OC(CC)CCCCC MAHDKHLSBQARSK-NXVVXOECSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- KPWVUBSQUODFPP-UHFFFAOYSA-N ethenyl-(ethenyl-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C=C)O[Si](C)(C=C)C1=CC=CC=C1 KPWVUBSQUODFPP-UHFFFAOYSA-N 0.000 description 1
- HOMYFVKFSFMSFF-UHFFFAOYSA-N ethenyl-[ethenyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=C)O[Si](C=C)(C=1C=CC=CC=1)C1=CC=CC=C1 HOMYFVKFSFMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005417 glycidoxyalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052950 sphalerite Inorganic materials 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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Abstract
Description
(A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素原子を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素原子-結合水素原子0.1~10.0モルが与えられるような量での);
(C)ヒドロシリル化触媒(組成物の硬化を促進するのに十分な量での);
(D)マレイン酸エステル化合物(質量単位によって組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル以外のヒドロシリル化阻害剤(質量単位によって組成物に対して200~20,000ppmの量での)を含む。
(A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素原子を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素-結合水素原子0.1~10.0モルが与えられるような量での);
(C)ヒドロシリル化触媒(組成物の硬化を促進するのに十分な量での);
(D)マレイン酸エステル化合物(質量単位によって組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル化合物以外のヒドロシリル化反応阻害剤(質量単位によって組成物に対して200~20,000ppmの量での)
を含む。
ViMe2SiO(Me2SiO)xSiMe2Vi
ViPhMeSiO(Me2SiO)xSiMePhVi
ViPh2SiO(Me2SiO)xSiPh2Vi
ViMe2SiO(Me2SiO)x(Ph2SiO)x’SiMe2Vi
ViPhMeSiO(Me2SiO)x(Ph2SiO)x’SiPhMeVi
ViPh2SiO(Me2SiO)x(Ph2SiO)x’SiPh2Vi
ViMe2SiO(MePhSiO)xSiMe2Vi
MePhViSiO(MePhSiO)xSiMePhVi
Ph2ViSiO(MePhSiO)xSiPh2Vi
ViMe2SiO(Ph2SiO)x(PhMeSiO)x’SiMe2Vi
ViPhMeSiO(Ph2SiO)x(PhMeSiO)x’SiPhMeVi
ViPh2SiO(Ph2SiO)x(PhMeSiO)x’SiPh2Vi
HMe2SiO(Ph2SiO)ySiMe2H
HMePhSiO(Ph2SiO)ySiMePhH
HMeNaphSiO(Ph2SiO)ySiMeNaphH
HMePhSiO(Ph2SiO)y(MePhSiO)y’SiMePhH
HMePhSiO(Ph2SiO)y(Me2SiO)y’SiMePhH
(HMe2SiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(NaphSiO3/2)d
(HMe2SiO1/2)c(NaphSiO3/2)d
(HMePhSiO1/2)c(HMe2SiO1/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(NaphSiO3/2)f
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(PhSiO3/2)f
ヒドロシリル化-硬化性シリコーン組成物の貯蔵安定性は、示差走査熱量測定計(DSC7000;SII Nanotechnologyにより製造された)を使用して、10℃/分の加熱速度で測定された熱発生ピーク温度(℃)に基づいて評価した。
ヒドロシリル化-硬化性シリコーン組成物の硬化性は、レオメータMDR 2000(Alpha Technologies,Ltd.により製造された)を使用して評価した。硬化温度は、150℃であった。測定のために、1%トルク値を得るのに要した時間(分)を、Ts1で示し、90%トルク値を得るのに要した時間(分)を、T90で示した。
5gのヒドロシリル化-硬化性シリコーン組成物を直径60mmのアルミニウムペトリ皿に注ぎ入れ、150℃で1時間加熱することによって硬化性生成物を形成させた。硬化生成物の外観を以下のとおり視覚的に観察した。
N:しわが観察されなかった。
Y:しわが観察された。
以下の成分を、表1~表5に示される組成(質量部)に従って一様に混合して、実施例1~実施例14及び比較例1~比較例16のヒドロシリル化-硬化性シリコーン組成物を調製した。式において、「Me」、「Vi」、「Ph」、及び「Ep」は、それぞれ、メチル基、ビニル基、フェニル基、及び3-グリシドキシプロピル基を表す。さらに、表1~表5において、「SiH/Vi」は、ヒドロシリル化-硬化性シリコーン組成物中の成分(A)中のビニル基1モル当たりの成分(B)中のケイ素-結合水素原子のモルを表す。
成分(a-1):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.25(PhSiO3/2)0.75
成分(a-2):以下の平均式によって表されるオルガノポリシロキサン:
Me2ViSiO(Me2SiO)200(Ph2SiO)50SiMe2Vi
成分(a-3):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.13(Me3SiO1/2)0.14(MeSiO3/2)0.53(PhSiO3/2)0.22
成分(a-4):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表される30質量%のオルガノポリシロキサン:
(Me3SiO1/2)0.47(Me2ViSiO1/2)0.05(SiO4/2)0.48
と、両分子末端にてジメチルビニルシロキシ基で末端化された70質量%のジメチルポリシロキサン(ビニル基の含有量=0.23質量%)との混合物。
成分(a-5):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.20(PhSiO3/2)0.80
成分(a-6):以下の平均式によって表されるオルガノポリシロキサン:
Me2ViSiO(MePhSiO)25SiMe2Vi
成分(a-7):以下の式によって表されるオルガノポリシロキサン:
(Me2ViSiO)4Si
成分(b-1):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
HMe2SiO(Ph2SiO)SiMe2H
成分(b-2):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
(Me2HSiO1/2)0.60(PhSiO3/2)0.40
成分(b-3):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
Me3SiO(MeHSiO)40SiMe3
成分(c-1):白金の1,3-ジビニルテトラメチルジシロキサン錯体の1,3-ジビニルテトラメチルジシロキサン溶液(白金金属含有量=おおよそ4,000ppm)
成分(d-1):ジアリルマレエート
成分(d-2):ビス(エチルヘキシル)マレエート
成分(e-1):1-エチニルシクロヘキサン-1-オール
成分(e-2):1,3,5,7-テトラメチル-1,3,5,7-テトラビニル-シクロテトラシロキサン
成分(f-1):以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.18(MeEpSiO2/2)0.28(PhSiO3/2)0.54
成分(g-1):1.4質量%のセリウム含有量を有するセリウム含有ジメチルポリシロキサン
成分(h-1):100m2/gのBET表面積を有するシリカ充填剤
以下の成分を、表1~表5に示される組成(質量部)に従って一様に混合して、実施例1~4及び実施例8~14及び比較例1~8及び比較例12~16のヒドロシリル化-硬化性シリコーン組成物を調製した(表3中の例は全ては参考例である)。式において、「Me」、「Vi」、「Ph」、及び「Ep」は、それぞれ、メチル基、ビニル基、フェニル基、及び3-グリシドキシプロピル基を表す。さらに、表1~表5において、「SiH/Vi」は、ヒドロシリル化-硬化性シリコーン組成物中の成分(A)中のビニル基1モル当たりの成分(B)中のケイ素-結合水素原子のモルを表す。
Claims (5)
- マレイン酸エステル化合物;及びマレイン酸エステル化合物以外のヒドロシリル化阻害剤を含むヒドロシリル化-硬化性シリコーン組成物であって;ここで、それぞれ、質量単位によって前記組成物に対して、前記マレイン酸エステルの含有量は、50~6,000ppmの量であり、前記ヒドロシリル化阻害剤の含有量は、200~20,000ppmの量である、ヒドロシリル化-硬化性シリコーン組成物。
- (A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素-結合水素原子0.1~10.0モルが与えられるような量での);
(C)ヒドロシリル化触媒(前記組成物の硬化を促進するために十分な量での);
(D)マレイン酸エステル化合物(質量単位によって前記組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル化合物以外のヒドロシリル化阻害剤(質量単位によって前記組成物に対して200~20,000ppmの量での)を含む、請求項1に記載のヒドロシリル化-硬化性シリコーン組成物。 - (F)接着促進剤(成分(A)~成分(E)の100質量部当たり0.01~50質量部の量での)をさらに含む、請求項2に記載のヒドロシリル化-硬化性シリコーン組成物。
- (G)セリウム含有オルガノポリシロキサン(この成分中のセリウム原子の量が、質量単位によって前記組成物に対して10~2,000ppmであるような量での)をさらに含む、請求項2又は3に記載のヒドロシリル化-硬化性シリコーン組成物。
- 光学半導体素子のためのシーリング、コーティング、又は接着剤である、請求項1~4のいずれか一項に記載のヒドロシリル化-硬化性オルガノポリシロキサン組成物。
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